# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10007
_database_code_depnum_ccdc_archive 'CCDC 1905056'
loop_
_audit_author_name
_audit_author_address
'Ruediger W. Seidel'
;Martin-Luther-Universitaet Halle-Wittenberg
Germany
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        furan-2-carbaldehyde
_chemical_name_common            furfural
_chemical_melting_point          236
_chemical_formula_moiety         'C5 H4 O2'
_chemical_formula_sum            'C5 H4 O2'
_chemical_formula_weight         96.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9261(19)
_cell_length_b                   11.402(3)
_cell_length_c                   15.557(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1406.0(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2812
_cell_measurement_theta_min      5.6877
_cell_measurement_theta_max      41.2538

_exptl_crystal_description       cylinder
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.343
_exptl_crystal_size_mid          0.522
_exptl_crystal_size_min          0.501
_exptl_crystal_size_rad          0.250
_exptl_absorpt_coefficient_mu    0.905
_shelx_estimated_absorpt_T_min   0.376
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.47992
_exptl_absorpt_correction_T_max  0.70460
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            56988
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.808
_diffrn_reflns_theta_max         68.001
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2485
_reflns_number_gt                2336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.980

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2018)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.4655P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 946 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2485
_refine_ls_number_parameters     227
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.1991(3) 0.30354(19) 0.43865(12) 0.0349(5) Uani 1 1 d . . . . .
O2_1 O 0.5009(3) 0.3172(3) 0.34244(16) 0.0603(8) Uani 1 1 d . . . . .
C2_1 C 0.2045(4) 0.3006(3) 0.35071(18) 0.0319(6) Uani 1 1 d . . . . .
C3_1 C 0.0460(4) 0.2937(3) 0.3180(2) 0.0378(7) Uani 1 1 d D . . . .
H3_1 H 0.017(5) 0.292(3) 0.2583(17) 0.045 Uiso 1 1 d D U . . .
C4_1 C -0.0653(4) 0.2926(3) 0.3895(2) 0.0404(7) Uani 1 1 d D . . . .
H4_1 H -0.184(3) 0.292(3) 0.388(2) 0.049 Uiso 1 1 d D U . . .
C5_1 C 0.0325(4) 0.2979(3) 0.4601(2) 0.0394(7) Uani 1 1 d D . . . .
H5_1 H 0.006(5) 0.299(3) 0.5221(18) 0.047 Uiso 1 1 d D U . . .
C6_1 C 0.3643(4) 0.3098(3) 0.3075(2) 0.0443(8) Uani 1 1 d D . . . .
H6_1 H 0.349(5) 0.312(3) 0.2436(17) 0.053 Uiso 1 1 d D U . . .
O1_2 O 0.2698(2) 0.68947(18) 0.44253(12) 0.0333(5) Uani 1 1 d . . . . .
O2_2 O 0.5721(3) 0.6327(2) 0.35585(16) 0.0510(6) Uani 1 1 d . . . . .
C2_2 C 0.2746(4) 0.6320(2) 0.36489(18) 0.0321(6) Uani 1 1 d . . . . .
C3_2 C 0.1145(4) 0.6065(3) 0.3389(2) 0.0357(7) Uani 1 1 d D . . . .
H3_2 H 0.089(4) 0.567(3) 0.2850(18) 0.043 Uiso 1 1 d D U . . .
C4_2 C 0.0050(4) 0.6507(3) 0.4031(2) 0.0389(7) Uani 1 1 d D . . . .
H4_2 H -0.114(3) 0.647(3) 0.402(2) 0.047 Uiso 1 1 d D U . . .
C5_2 C 0.1035(4) 0.6997(3) 0.4638(2) 0.0372(7) Uani 1 1 d D . . . .
H5_2 H 0.078(5) 0.741(3) 0.5180(19) 0.045 Uiso 1 1 d D U . . .
C6_2 C 0.4338(4) 0.6093(3) 0.3251(2) 0.0411(7) Uani 1 1 d D . . . .
H6_2 H 0.421(5) 0.571(3) 0.2682(18) 0.049 Uiso 1 1 d D U . . .
O1_3 O 0.1068(3) 0.96429(19) 0.31848(13) 0.0363(5) Uani 1 1 d . . . . .
O2_3 O -0.2279(3) 0.9898(2) 0.37098(15) 0.0487(6) Uani 1 1 d . . . . .
C2_3 C 0.0641(3) 0.9941(2) 0.40117(18) 0.0296(6) Uani 1 1 d . . . . .
C3_3 C 0.2051(4) 1.0070(3) 0.44896(19) 0.0355(6) Uani 1 1 d D . . . .
H3_3 H 0.212(4) 1.030(3) 0.5085(17) 0.043 Uiso 1 1 d D U . . .
C4_3 C 0.3447(4) 0.9847(3) 0.3941(2) 0.0386(7) Uani 1 1 d D . . . .
H4_3 H 0.460(4) 0.983(3) 0.409(2) 0.046 Uiso 1 1 d D U . . .
C5_3 C 0.2792(4) 0.9593(3) 0.3169(2) 0.0393(7) Uani 1 1 d D . . . .
H5_3 H 0.326(5) 0.937(3) 0.2603(18) 0.047 Uiso 1 1 d D U . . .
C6_3 C -0.1125(4) 1.0058(3) 0.4220(2) 0.0366(7) Uani 1 1 d D . . . .
H6_3 H -0.135(4) 1.027(3) 0.4836(18) 0.044 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1_1 C5_1 1.363(4) . ?
O1_1 C2_1 1.369(3) . ?
O2_1 C6_1 1.215(4) . ?
C2_1 C3_1 1.357(4) . ?
C2_1 C6_1 1.438(4) . ?
C3_1 C4_1 1.420(5) . ?
C3_1 H3_1 0.96(3) . ?
C4_1 C5_1 1.345(5) . ?
C4_1 H4_1 0.94(3) . ?
C5_1 H5_1 0.99(3) . ?
C6_1 H6_1 1.00(3) . ?
O1_2 C5_2 1.364(4) . ?
O1_2 C2_2 1.374(3) . ?
O2_2 C6_2 1.225(4) . ?
C2_2 C3_2 1.363(4) . ?
C2_2 C6_2 1.430(4) . ?
C3_2 C4_2 1.417(5) . ?
C3_2 H3_2 0.97(3) . ?
C4_2 C5_2 1.346(5) . ?
C4_2 H4_2 0.94(3) . ?
C5_2 H5_2 0.99(3) . ?
C6_2 H6_2 0.99(3) . ?
O1_3 C5_3 1.368(4) . ?
O1_3 C2_3 1.373(3) . ?
O2_3 C6_3 1.225(4) . ?
C2_3 C3_3 1.351(4) . ?
C2_3 C6_3 1.443(4) . ?
C3_3 C4_3 1.420(4) . ?
C3_3 H3_3 0.97(3) . ?
C4_3 C5_3 1.340(5) . ?
C4_3 H4_3 0.94(3) . ?
C5_3 H5_3 0.99(3) . ?
C6_3 H6_3 1.01(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5_1 O1_1 C2_1 105.9(2) . . ?
C3_1 C2_1 O1_1 110.3(3) . . ?
C3_1 C2_1 C6_1 130.1(3) . . ?
O1_1 C2_1 C6_1 119.5(3) . . ?
C2_1 C3_1 C4_1 106.4(3) . . ?
C2_1 C3_1 H3_1 126(2) . . ?
C4_1 C3_1 H3_1 128(2) . . ?
C5_1 C4_1 C3_1 106.3(3) . . ?
C5_1 C4_1 H4_1 127(2) . . ?
C3_1 C4_1 H4_1 127(2) . . ?
C4_1 C5_1 O1_1 111.2(3) . . ?
C4_1 C5_1 H5_1 133(2) . . ?
O1_1 C5_1 H5_1 116(2) . . ?
O2_1 C6_1 C2_1 125.5(3) . . ?
O2_1 C6_1 H6_1 123(2) . . ?
C2_1 C6_1 H6_1 111(2) . . ?
C5_2 O1_2 C2_2 106.3(2) . . ?
C3_2 C2_2 O1_2 109.7(3) . . ?
C3_2 C2_2 C6_2 130.9(3) . . ?
O1_2 C2_2 C6_2 119.4(3) . . ?
C2_2 C3_2 C4_2 106.5(3) . . ?
C2_2 C3_2 H3_2 123(2) . . ?
C4_2 C3_2 H3_2 130(2) . . ?
C5_2 C4_2 C3_2 106.7(3) . . ?
C5_2 C4_2 H4_2 128(2) . . ?
C3_2 C4_2 H4_2 126(2) . . ?
C4_2 C5_2 O1_2 110.8(3) . . ?
C4_2 C5_2 H5_2 133(2) . . ?
O1_2 C5_2 H5_2 116(2) . . ?
O2_2 C6_2 C2_2 125.5(3) . . ?
O2_2 C6_2 H6_2 122(2) . . ?
C2_2 C6_2 H6_2 112(2) . . ?
C5_3 O1_3 C2_3 105.8(2) . . ?
C3_3 C2_3 O1_3 109.8(2) . . ?
C3_3 C2_3 C6_3 132.0(3) . . ?
O1_3 C2_3 C6_3 118.2(3) . . ?
C2_3 C3_3 C4_3 107.1(3) . . ?
C2_3 C3_3 H3_3 127(2) . . ?
C4_3 C3_3 H3_3 125(2) . . ?
C5_3 C4_3 C3_3 106.0(3) . . ?
C5_3 C4_3 H4_3 126(2) . . ?
C3_3 C4_3 H4_3 128(2) . . ?
C4_3 C5_3 O1_3 111.3(3) . . ?
C4_3 C5_3 H5_3 135(2) . . ?
O1_3 C5_3 H5_3 114(2) . . ?
O2_3 C6_3 C2_3 124.4(3) . . ?
O2_3 C6_3 H6_3 121(2) . . ?
C2_3 C6_3 H6_3 114(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C6_1 O2_1 2.0(6) . . . . ?
O1_2 C2_2 C6_2 O2_2 3.1(5) . . . . ?
O1_3 C2_3 C6_3 O2_3 0.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4_1 H4_1 O2_1 0.94(3) 2.61(3) 3.527(4) 165(3) 1_455 yes
C5_1 H5_1 O2_1 0.99(3) 2.49(3) 3.351(4) 146(3) 4_456 yes
C3_2 H3_2 O1_3 0.97(3) 2.52(3) 3.420(4) 153(3) 3_545 yes
C4_2 H4_2 O2_2 0.94(3) 2.60(3) 3.515(4) 165(3) 1_455 yes
C5_2 H5_2 O2_2 0.99(3) 2.43(3) 3.404(4) 167(3) 4_466 yes
C5_2 H5_2 O1_2 0.99(3) 2.64(3) 3.274(4) 122(3) 4_466 yes
C4_3 H4_3 O2_3 0.94(3) 2.54(3) 3.407(4) 153(3) 1_655 yes
C5_3 H5_3 O2_1 0.99(3) 2.51(3) 3.437(4) 156(3) 3_655 yes
C6_3 H6_3 O1_1 1.01(3) 2.63(3) 3.414(4) 135(3) 4_466 yes

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10328
_database_code_depnum_ccdc_archive 'CCDC 1905057'
loop_
_audit_author_name
_audit_author_address
'Ruediger W. Seidel'
;Martin-Luther-Universitaet Halle-Wittenberg
Germany
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1-(2-furyl)methylamine
_chemical_name_common            furfurylamine
_chemical_melting_point          203
_chemical_formula_moiety         'C5 H7 N O'
_chemical_formula_sum            'C5 H7 N O'
_chemical_formula_weight         97.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8006(13)
_cell_length_b                   7.8838(18)
_cell_length_c                   11.355(3)
_cell_angle_alpha                94.479(4)
_cell_angle_beta                 92.173(4)
_cell_angle_gamma                96.464(4)
_cell_volume                     513.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8059
_cell_measurement_theta_min      3.0489
_cell_measurement_theta_max      24.7576

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_crystal_size_rad          0.250
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_source                   'microfocus X-ray tube'
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            32754
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         36.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4869
_reflns_number_gt                3729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2018)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²+0.6587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4869
_refine_ls_number_parameters     157
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2524
_refine_ls_wR_factor_gt          0.2381
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.4975(3) 0.2023(2) 0.06934(13) 0.0249(3) Uani 1 1 d . . . . .
N1_1 N 0.6631(3) 0.3315(2) 0.33354(13) 0.0192(3) Uani 1 1 d D . . . .
H1A_1 H 0.679(5) 0.219(2) 0.317(3) 0.023 Uiso 1 1 d D U . . .
H1B_1 H 0.521(3) 0.341(4) 0.364(2) 0.023 Uiso 1 1 d D U . . .
C2_1 C 0.4793(3) 0.3547(2) 0.13314(14) 0.0173(3) Uani 1 1 d . . . . .
C3_1 C 0.2814(3) 0.4167(2) 0.09834(16) 0.0216(3) Uani 1 1 d D . . . .
H3_1 H 0.226(5) 0.522(3) 0.126(3) 0.026 Uiso 1 1 d D U . . .
C4_1 C 0.1696(3) 0.2967(3) 0.00691(16) 0.0231(3) Uani 1 1 d D . . . .
H4_1 H 0.009(4) 0.304(4) -0.031(3) 0.028 Uiso 1 1 d D U . . .
C5_1 C 0.3059(4) 0.1706(3) -0.00700(16) 0.0248(4) Uani 1 1 d D . . . .
H5_1 H 0.295(6) 0.066(3) -0.057(3) 0.030 Uiso 1 1 d D U . . .
C6_1 C 0.6675(3) 0.4171(2) 0.22332(15) 0.0213(3) Uani 1 1 d . . . . .
H6A_1 H 0.818246 0.404656 0.187411 0.026 Uiso 1 1 calc R U . . .
H6B_1 H 0.661085 0.540871 0.243331 0.026 Uiso 1 1 calc R U . . .
O1_2 O 0.9145(3) 0.98354(17) 0.31942(12) 0.0216(3) Uani 1 1 d . . . . .
N1_2 N 0.7956(3) 0.64833(19) 0.52928(13) 0.0179(3) Uani 1 1 d D . . . .
H1A_2 H 0.941(3) 0.662(4) 0.563(2) 0.021 Uiso 1 1 d D U . . .
H1B_2 H 0.786(5) 0.549(3) 0.481(2) 0.021 Uiso 1 1 d D U . . .
C2_2 C 0.9350(3) 0.8376(2) 0.37574(13) 0.0156(3) Uani 1 1 d . . . . .
C3_2 C 1.1253(3) 0.7667(2) 0.34100(15) 0.0184(3) Uani 1 1 d D . . . .
H3_2 H 1.178(5) 0.664(3) 0.367(3) 0.022 Uiso 1 1 d D U . . .
C4_2 C 1.2333(3) 0.8752(2) 0.25811(15) 0.0217(3) Uani 1 1 d D . . . .
H4_2 H 1.381(5) 0.857(4) 0.214(3) 0.026 Uiso 1 1 d D U . . .
C5_2 C 1.0999(4) 1.0032(3) 0.24816(16) 0.0236(3) Uani 1 1 d D . . . .
H5_2 H 1.116(6) 1.103(3) 0.205(3) 0.028 Uiso 1 1 d D U . . .
C6_2 C 0.7537(3) 0.7923(2) 0.46180(14) 0.0173(3) Uani 1 1 d . . . . .
H6A_2 H 0.743619 0.893760 0.517721 0.021 Uiso 1 1 calc R U . . .
H6B_2 H 0.601499 0.765130 0.417973 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1_1 C2_1 1.371(2) . ?
O1_1 C5_1 1.371(2) . ?
N1_1 C6_1 1.467(2) . ?
N1_1 H1A_1 0.905(17) . ?
N1_1 H1B_1 0.915(17) . ?
C2_1 C3_1 1.354(3) . ?
C2_1 C6_1 1.483(2) . ?
C3_1 C4_1 1.432(3) . ?
C3_1 H3_1 0.96(2) . ?
C4_1 C5_1 1.342(3) . ?
C4_1 H4_1 1.02(2) . ?
C5_1 H5_1 0.96(2) . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
O1_2 C5_2 1.372(3) . ?
O1_2 C2_2 1.374(2) . ?
N1_2 C6_2 1.456(2) . ?
N1_2 H1A_2 0.905(17) . ?
N1_2 H1B_2 0.915(17) . ?
C2_2 C3_2 1.350(3) . ?
C2_2 C6_2 1.495(2) . ?
C3_2 C4_2 1.435(2) . ?
C3_2 H3_2 0.96(2) . ?
C4_2 C5_2 1.348(3) . ?
C4_2 H4_2 1.02(2) . ?
C5_2 H5_2 0.95(2) . ?
C6_2 H6A_2 0.9900 . ?
C6_2 H6B_2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2_1 O1_1 C5_1 106.69(15) . . ?
C6_1 N1_1 H1A_1 109.0(18) . . ?
C6_1 N1_1 H1B_1 107.3(18) . . ?
H1A_1 N1_1 H1B_1 109(3) . . ?
C3_1 C2_1 O1_1 109.61(15) . . ?
C3_1 C2_1 C6_1 133.30(17) . . ?
O1_1 C2_1 C6_1 117.09(16) . . ?
C2_1 C3_1 C4_1 106.85(17) . . ?
C2_1 C3_1 H3_1 128.1(18) . . ?
C4_1 C3_1 H3_1 125.0(18) . . ?
C5_1 C4_1 C3_1 106.24(16) . . ?
C5_1 C4_1 H4_1 129.0(18) . . ?
C3_1 C4_1 H4_1 124.5(18) . . ?
C4_1 C5_1 O1_1 110.60(16) . . ?
C4_1 C5_1 H5_1 133.7(19) . . ?
O1_1 C5_1 H5_1 115.7(19) . . ?
N1_1 C6_1 C2_1 116.23(14) . . ?
N1_1 C6_1 H6A_1 108.2 . . ?
C2_1 C6_1 H6A_1 108.2 . . ?
N1_1 C6_1 H6B_1 108.2 . . ?
C2_1 C6_1 H6B_1 108.2 . . ?
H6A_1 C6_1 H6B_1 107.4 . . ?
C5_2 O1_2 C2_2 106.45(15) . . ?
C6_2 N1_2 H1A_2 111.3(18) . . ?
C6_2 N1_2 H1B_2 110.8(17) . . ?
H1A_2 N1_2 H1B_2 105(3) . . ?
C3_2 C2_2 O1_2 110.16(15) . . ?
C3_2 C2_2 C6_2 133.66(15) . . ?
O1_2 C2_2 C6_2 116.16(15) . . ?
C2_2 C3_2 C4_2 106.54(16) . . ?
C2_2 C3_2 H3_2 126.4(18) . . ?
C4_2 C3_2 H3_2 127.0(18) . . ?
C5_2 C4_2 C3_2 106.37(17) . . ?
C5_2 C4_2 H4_2 127.0(17) . . ?
C3_2 C4_2 H4_2 126.7(17) . . ?
C4_2 C5_2 O1_2 110.47(15) . . ?
C4_2 C5_2 H5_2 132(2) . . ?
O1_2 C5_2 H5_2 117(2) . . ?
N1_2 C6_2 C2_2 114.50(14) . . ?
N1_2 C6_2 H6A_2 108.6 . . ?
C2_2 C6_2 H6A_2 108.6 . . ?
N1_2 C6_2 H6B_2 108.6 . . ?
C2_2 C6_2 H6B_2 108.6 . . ?
H6A_2 C6_2 H6B_2 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C6_1 N1_1 -76.2(2) . . . . ?
O1_2 C2_2 C6_2 N1_2 -173.42(13) . . . . ?
C3_1 C2_1 C6_1 N1_1 103.1(2) . . . . ?
C3_2 C2_2 C6_2 N1_2 4.8(3) . . . . ?
C2_1 C6_1 N1_1 H1A_1 62(2) . . . . ?
C2_1 C6_1 N1_1 H1B_1 -56.3(19) . . . . ?
C2_2 C6_2 N1_2 H1A_2 51(2) . . . . ?
C2_2 C6_2 N1_2 H1B_2 -66(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1_1 H1A_1 O1_2 0.905(17) 2.43(2) 3.245(2) 150(2) 1_545 yes
N1_1 H1B_1 N1_2 0.915(17) 2.243(18) 3.147(2) 170(2) 2_666 yes
N1_2 H1A_2 N1_1 0.905(17) 2.532(17) 3.433(2) 173(2) 2_766 yes
N1_2 H1B_2 N1_1 0.915(17) 2.332(18) 3.216(2) 162(2) . yes
C5_1 H5_1 O1_1 0.96(2) 2.54(3) 3.307(3) 136(2) 2_655 yes

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.092


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10922
_database_code_depnum_ccdc_archive 'CCDC 1905058'
loop_
_audit_author_name
_audit_author_address
'Ruediger W. Seidel'
;Martin-Luther-Universitaet Halle-Wittenberg
Germany
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        furan-2-carbonitrile
_chemical_name_common            2-furonitrile
_chemical_melting_point          184
_chemical_formula_moiety         'C5 H3 N O'
_chemical_formula_sum            'C5 H3 N O'
_chemical_formula_weight         93.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.2801(3)
_cell_length_b                   12.0768(7)
_cell_length_c                   7.2295(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.7880(10)
_cell_angle_gamma                90
_cell_volume                     455.59(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9299
_cell_measurement_theta_min      6.1944
_cell_measurement_theta_max      71.7999

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.116
_exptl_crystal_size_mid          0.771
_exptl_crystal_size_min          0.726
_exptl_crystal_size_rad          0.250
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   0.463
_shelx_estimated_absorpt_T_max   0.589
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.07349
_exptl_absorpt_correction_T_max  0.24513
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            10333
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         7.202
_diffrn_reflns_theta_max         72.022
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             870
_reflns_number_gt                867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2018)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.0818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.075(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         870
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.82622(14) 0.41660(7) 0.37214(11) 0.0346(3) Uani 1 1 d . . . . .
N1 N 0.9609(2) 0.34896(9) 0.83467(14) 0.0396(3) Uani 1 1 d . . . . .
C2 C 0.6991(2) 0.37342(9) 0.50734(16) 0.0303(3) Uani 1 1 d . . . . .
C3 C 0.4523(2) 0.35112(10) 0.43712(16) 0.0333(3) Uani 1 1 d . . . . .
H3 H 0.332(3) 0.3228(12) 0.5040(19) 0.040 Uiso 1 1 d . U . . .
C4 C 0.4211(2) 0.38160(10) 0.24570(17) 0.0348(4) Uani 1 1 d . . . . .
H4 H 0.268(3) 0.3774(12) 0.154(2) 0.042 Uiso 1 1 d . U . . .
C5 C 0.6496(2) 0.41983(10) 0.21401(16) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.711(3) 0.4478(13) 0.104(2) 0.044 Uiso 1 1 d . U . . .
C6 C 0.8446(2) 0.35993(9) 0.68821(15) 0.0324(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3610(14) . ?
O1 C2 1.3705(14) . ?
N1 C6 1.1478(15) . ?
C2 C3 1.3517(16) . ?
C2 C6 1.4210(15) . ?
C3 C4 1.4170(17) . ?
C3 H3 0.923(15) . ?
C4 C5 1.3438(17) . ?
C4 H4 0.967(16) . ?
C5 H5 0.962(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 105.23(9) . . ?
C3 C2 O1 110.92(10) . . ?
C3 C2 C6 132.64(11) . . ?
O1 C2 C6 116.44(9) . . ?
C2 C3 C4 106.05(11) . . ?
C2 C3 H3 125.5(9) . . ?
C4 C3 H3 128.4(9) . . ?
C5 C4 C3 106.41(10) . . ?
C5 C4 H4 125.6(9) . . ?
C3 C4 H4 128.0(9) . . ?
C4 C5 O1 111.39(10) . . ?
C4 C5 H5 133.2(9) . . ?
O1 C5 H5 115.4(9) . . ?
N1 C6 C2 179.66(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 N1 0.967(16) 2.632(16) 3.5614(15) 161.2(13) 1_454 yes

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9966
_database_code_depnum_ccdc_archive 'CCDC 1905059'
loop_
_audit_author_name
_audit_author_address
'Ruediger W. Seidel'
;Martin-Luther-Universitaet Halle-Wittenberg
Germany
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-methylfuran
_chemical_name_common            ?
_chemical_melting_point          184
_chemical_formula_moiety         'C5 H6 O'
_chemical_formula_sum            'C5 H6 O'
_chemical_formula_weight         82.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           106
_space_group_name_H-M_alt        'P 42 b c'
_space_group_name_Hall           'P 4c -2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   12.4727(15)
_cell_length_b                   12.4727(15)
_cell_length_c                   6.0594(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     942.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1990
_cell_measurement_theta_min      3.5436
_cell_measurement_theta_max      41.1263

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_crystal_size_rad          0.250
_exptl_absorpt_coefficient_mu    0.643
_shelx_estimated_absorpt_T_min   0.566
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.59579
_exptl_absorpt_correction_T_max  0.77536
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'MONTEL graded multilayer optic'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            36611
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.014
_diffrn_reflns_theta_max         68.061
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             852
_reflns_number_gt                839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2018)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+0.1207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         852
_refine_ls_number_parameters     66
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0509
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22075(7) 0.53212(6) 0.5752(2) 0.0254(3) Uani 1 1 d . . . . .
C2 C 0.28355(9) 0.44181(9) 0.5550(3) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.25921(11) 0.39071(11) 0.3662(3) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.2915(13) 0.3277(13) 0.312(3) 0.032 Uiso 1 1 d . U . . .
C4 C 0.17664(11) 0.45143(11) 0.2598(3) 0.0277(3) Uani 1 1 d . . . . .
H4 H 0.1437(13) 0.4366(12) 0.124(3) 0.033 Uiso 1 1 d . U . . .
C5 C 0.15647(11) 0.53515(11) 0.3910(3) 0.0277(3) Uani 1 1 d . . . . .
H5 H 0.1087(14) 0.5949(14) 0.381(3) 0.033 Uiso 1 1 d . U . . .
C6 C 0.35906(11) 0.42186(13) 0.7391(3) 0.0339(4) Uani 1 1 d . . . . .
H6A H 0.405063 0.360672 0.702645 0.051 Uiso 1 1 calc R U . . .
H6B H 0.318554 0.406097 0.873819 0.051 Uiso 1 1 calc R U . . .
H6C H 0.403540 0.485615 0.762646 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.375(2) . ?
O1 C2 1.3774(15) . ?
C2 C3 1.344(2) . ?
C2 C6 1.481(2) . ?
C3 C4 1.432(2) . ?
C3 H3 0.942(17) . ?
C4 C5 1.336(2) . ?
C4 H4 0.938(19) . ?
C5 H5 0.96(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C2 106.38(11) . . ?
C3 C2 O1 109.57(12) . . ?
C3 C2 C6 134.83(13) . . ?
O1 C2 C6 115.59(13) . . ?
C2 C3 C4 107.15(12) . . ?
C2 C3 H3 126.5(9) . . ?
C4 C3 H3 126.3(9) . . ?
C5 C4 C3 106.32(13) . . ?
C5 C4 H4 126.4(9) . . ?
C3 C4 H4 127.3(9) . . ?
C4 C5 O1 110.59(12) . . ?
C4 C5 H5 133.6(11) . . ?
O1 C5 H5 115.8(11) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H6A C6 C2 O1 -174.1 . . . . ?
H6B C6 C2 O1 65.9 . . . . ?
H6C C6 C2 O1 -54.1 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O1 0.96(2) 2.611(19) 3.3804(18) 137.8(15) 8_454 yes

_refine_diff_density_max         0.087
_refine_diff_density_min         -0.078
_refine_diff_density_rms         0.019


_exptl_crystal_recrystallization_method 'From the Melt'
